Thiopyran derivative, polymer, resist composition, and method for manufacturing semiconductor device using such resist composition

Abstract

To provide a thiopyran derivative, having a structure expressed by the following general formula 1: where X is O or S; R 1 is —H, —CH 3 , C2-4 alkyl group, thioether group, or ketone group; R 2 is —H, —CH 3 , or trifluoromethyl group; and R 1 and R 2 may be identical to or different from each other.

1. A thiopyran derivative, having a structure expressed by the following general formula 1: 
       
         
           
           
               
               
           
         
         where X is O or S; R 1  is —H, —CH 3 , C2-4 alkyl group, thioether group, or ketone group; R 2  is —H, —CH 3 , or trifluoromethyl group; and R 1  and R 2  may be identical to or different from each other. 
       
     
     
       2. A polymer, comprising:
 a monomer unit containing a thiopyran derivative, 
 wherein the thiopyran derivative has a structure expressed by the following general formula 1: 
 
       
         
           
           
               
               
           
         
         where X is O or S; R 1  is —H, —CH 3 , C2-4 alkyl group, thioether group, or ketone group; R 2  is —H, —CH 3 , or trifluoromethyl group; and R 1  and R 2  may be identical to or different from each other. 
       
     
     
       3. The polymer according to  claim 2 , further comprising a monomer unit containing an acid labile group. 
     
     
       4. The polymer according to  claim 3 , wherein the acid labile group is a 2-alkyladamanthyl group. 
     
     
       5. The polymer according to  claim 2 , further comprising a monomer unit containing a lactone derivative. 
     
     
       6. The polymer according to  claim 2 , wherein an amount of the monomer unit containing the thiopyran derivative contained in the polymer is 10 mol % to 55 mol %. 
     
     
       7. A resist composition, comprising:
 a polymer comprising a monomer unit containing a thiopyran derivative having a structure expressed by the following general formula 1: 
 
       
         
           
           
               
               
           
         
         where X is O or S; R 1  is —H, —CH 3 , C2-4 alkyl group, thioether group, or ketone group; R 2  is —H, —CH 3 , or trifluoromethyl group; and R 1  and R 2  may be identical to or different from each other. 
       
     
     
       8. The resist composition according to  claim 7 , wherein the resist composition has a refractive index of 1.520 or more with respect to light having a wavelength of 400 nm to 850 nm. 
     
     
       9. The resist composition according to  claim 7 , wherein the polymer is an acrylic resin. 
     
     
       10. The resist composition according to  claim 7 , further comprising an acid-generating agent. 
     
     
       11. The resist composition according to  claim 7 , further comprising a monomer of a thiopyran derivative,
 wherein the thiopyran derivative has a structure expressed by the following general formula 1: 
 
       
         
           
           
               
               
           
         
         where X is O or S; R 1  is —H, —CH 3 , C2-4 alkyl group, thioether group, or ketone group; R 2  is —H, —CH 3 , or trifluoromethyl group; and R 1  and R 2  may be identical to or different from each other. 
       
     
     
       12. The resist composition according to  claim 7 , further comprising a homopolymer of a thiopyran derivative,
 wherein the thiopyran derivative has a structure expressed by the following general formula 1: 
 
       
         
           
           
               
               
           
         
         where X is O or S; R 1  is —H, —CH 3 , C2-4 alkyl group, thioether group, or ketone group; R 2  is —H, —CH 3 , or trifluoromethyl group; and R 1  and R 2  may be identical to or different from each other.